Hydrochloric Acid → HCID 68109234, compound

HRID 1429286Notes

Reaction equation

HRID 1429286 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][OH:11])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH:26]=[C:25]([OH:30])[CH:24]=[CH:23]3)O1.C(OCC)(=O)C.Cl>O.C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:11][CH2:10][C:9]#[C:8][C:5]1[CH:6]=[CH:7][C:2]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[CH:26]=[C:25]([OH:30])[CH:24]=[CH:23]3)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 40481813-(4-bromophenyl)prop-2-yn-1-olHCID 219239636-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol

Product 1

HCID 68109234HCID 68109234, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

13.0 g (0.047 mol) of sodium metaborate octahydrate are initially introduced in 100 ml of water, and a solution of 7.00 g (33.1 mmol) of 3-(4-bromophenyl)prop-2-yn-1-ol (CAS No. 37614-58-7) and 9.00 g (33.3 mmol) of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-ol (CAS No. 269410-21-1) in 200 ml of THF is added. After addition of 1.00 g (1.40 mmol) of bis(triphenylphosphine)palladium(II) chloride, the batch is heated under reflux for 5 h, 100 ml of ethyl acetate are subsequently added, and the mixture is acidified using 2 M hydrochloric acid. The org. phase is separated off, dried over sodium sulfate and evaporated. The residue is filtered through silica gel with toluene/ethyl acetate (3:2), and the crude product is recrystallised from toluene/ethyl acetate, giving 6-[4-(3-hydroxyprop-1-ynyl)phenyl]naphthalen-2-ol as a colourless solid.

Workup

  1. temperaturethe batch is heated
  2. temperatureunder reflux for 5 h
  3. customphase is separated off
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. filtrationThe residue is filtered through silica gel with toluene/ethyl acetate (3:2)
  7. customthe crude product is recrystallised from toluene/ethyl acetate

Sources & evidence

ORD record
ord-745c2223662b482aa229661fba9f05a7
Source dataset
uspto-grants-2015_01
Patent number
US08940184B2

Reaction notes

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